CA2870837C - 5-[[4-[[morpholin-2-yl]methylamino]-5-(trifluoromethyl)-2-pyridyl]amino]pyrazine-2-carbonitrile and therapeutic uses thereof - Google Patents

5-[[4-[[morpholin-2-yl]methylamino]-5-(trifluoromethyl)-2-pyridyl]amino]pyrazine-2-carbonitrile and therapeutic uses thereof Download PDF

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Publication number
CA2870837C
CA2870837C CA2870837A CA2870837A CA2870837C CA 2870837 C CA2870837 C CA 2870837C CA 2870837 A CA2870837 A CA 2870837A CA 2870837 A CA2870837 A CA 2870837A CA 2870837 C CA2870837 C CA 2870837C
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cancer
compound
treatment
inhibitor
chk1
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French (fr)
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CA2870837A1 (en
Inventor
Ian Collins
Thomas Peter Matthews
Tatiana FARIA DA FONSECA MCHARDY
James Osborne
Michael LAINCHBURY
Michael Ian WALTON
Michelle Dawn Garrett
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Cancer Research Technology Ltd
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Cancer Research Technology Ltd
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/4738Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4745Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/53751,4-Oxazines, e.g. morpholine
    • A61K31/53771,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Molecular Biology (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2870837A 2012-05-15 2013-05-14 5-[[4-[[morpholin-2-yl]methylamino]-5-(trifluoromethyl)-2-pyridyl]amino]pyrazine-2-carbonitrile and therapeutic uses thereof Active CA2870837C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261647200P 2012-05-15 2012-05-15
US61/647,200 2012-05-15
PCT/GB2013/051233 WO2013171470A1 (en) 2012-05-15 2013-05-14 5-[[4-[[morpholin-2-yl]methylamino]-5-(trifluoromethyl)-2-pyridyl]amino]pyrazine-2-carbonitrile and therapeutic uses thereof

Publications (2)

Publication Number Publication Date
CA2870837A1 CA2870837A1 (en) 2013-11-21
CA2870837C true CA2870837C (en) 2022-05-10

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CA2870837A Active CA2870837C (en) 2012-05-15 2013-05-14 5-[[4-[[morpholin-2-yl]methylamino]-5-(trifluoromethyl)-2-pyridyl]amino]pyrazine-2-carbonitrile and therapeutic uses thereof

Country Status (19)

Country Link
US (3) US9663503B2 (enExample)
EP (2) EP2855448B1 (enExample)
JP (2) JP6027230B2 (enExample)
KR (6) KR20240023685A (enExample)
CN (2) CN104302635B (enExample)
AU (2) AU2013261605B2 (enExample)
BR (1) BR112014026801B1 (enExample)
CA (1) CA2870837C (enExample)
DK (1) DK2855448T3 (enExample)
ES (2) ES2981584T3 (enExample)
IL (1) IL235133A (enExample)
IN (1) IN2014DN09221A (enExample)
MX (1) MX358819B (enExample)
NZ (1) NZ702050A (enExample)
PL (1) PL2855448T3 (enExample)
RU (1) RU2659786C2 (enExample)
SG (1) SG11201407238VA (enExample)
WO (1) WO2013171470A1 (enExample)
ZA (1) ZA201408452B (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6073910B2 (ja) 2011-11-09 2017-02-01 キャンサー・リサーチ・テクノロジー・リミテッド 5−(ピリジン−2−イル−アミノ)−ピラジン−2−カルボニトリル化合物及びその治療使用
JP6027230B2 (ja) * 2012-05-15 2016-11-16 キャンサー・リサーチ・テクノロジー・リミテッド 5−[[4−[[モルホリン−2−イル]メチルアミノ]−5−(トリフルオロメチル)−2−ピリジル]アミノ]ピラジン−2−カルボニトリルおよびその治療上の使用
SMT202000713T1 (it) 2012-12-07 2021-03-15 Vertex Pharma Pirazolo [1,5-a] pirimidine utili come inibitori dell'atr chinasi per il trattamento di malattie del cancro
JP2016512815A (ja) 2013-03-15 2016-05-09 バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated Atrキナーゼの阻害剤として有用な縮合ピラゾロピリミジン誘導体
HUE046727T2 (hu) 2013-12-06 2020-03-30 Vertex Pharma Az ATR-kináz inhibitoraként használható vegyület, 2-amino-6-fluoro-N-[5-fluoro-piridin-3-IL]-pirazolo-[1,5-A]-pirimidin-3-karboxamid, ennek elõállítása, különbözõ szilárd formái és ezek radioaktív nyomjelzett származékai
CN107074863B (zh) 2014-06-05 2019-12-03 沃泰克斯药物股份有限公司 Atr激酶抑制剂的制备方法及其不同的固体形式
PL3157566T3 (pl) * 2014-06-17 2019-10-31 Vertex Pharma Metoda leczenia nowotworu przy użyciu kombinacji inhibitorów chk1 i atr
KR102678021B1 (ko) 2015-09-30 2024-06-26 버텍스 파마슈티칼스 인코포레이티드 Dna 손상제와 병용되는, atr 저해제를 포함하는 암 치료용 약제학적 조성물
WO2018094325A1 (en) * 2016-11-18 2018-05-24 The Trustees Of Columbia University In The City Of New York Therapeutic modulation of oncogenes by pharmacologic top2 targeting for cancer
US20200108074A1 (en) * 2017-03-31 2020-04-09 Seattle Genetics, Inc. Combinations of chk1- and wee1- inhibitors
KR102645511B1 (ko) * 2017-04-10 2024-03-08 시에라 온코로지 엘엘씨 종양 성장을 저해하는 CHK1(SRA737)/PARPi 조합 방법
WO2018191299A1 (en) * 2017-04-10 2018-10-18 Sierra Oncology, Inc. Chk1(sra737)wee1 inhibitor combination methods of inhibiting tumor growth
AU2018278336A1 (en) * 2017-06-01 2020-01-16 Crt Pioneer Fund Lp Biomarkers and patient selection strategies
CN107266897B (zh) * 2017-08-04 2019-05-14 上海跃贝新材料科技股份有限公司 一种低粘度矿物增强pc/pet合金材料及其制备方法
AU2019224164A1 (en) * 2018-02-26 2020-10-01 Crt Pioneer Fund Lp Methods of treatment of cancer comprising Chk1 inhibitors
JP2022523028A (ja) * 2019-01-25 2022-04-21 ヌメディー, インコーポレイテッド 特発性肺線維症を処置するための方法
CA3135165A1 (en) * 2019-03-28 2020-10-01 Sierra Oncology, Inc. Methods of treating cancer with chk1 inhibitors
WO2020232154A2 (en) * 2019-05-14 2020-11-19 Sierra Oncology, Inc. Methods of treating cancer using chk1 inhibitors
CN110872277B (zh) * 2019-11-14 2021-06-04 浙江大学 N-取代芳环-2-氨基嘧啶类化合物及用途
CN110680928B (zh) * 2019-12-06 2020-04-28 深圳前海港影生物科技有限公司 抑制黑色素合成的偶联物及其在药品和化妆品中的应用
CN110684083B (zh) * 2019-12-06 2020-05-15 北京诺赛启研再生医学研究院有限公司 抑制黑色素合成的偶联物ii及其在药品和化妆品中的应用
TW202204348A (zh) * 2020-04-07 2022-02-01 美商西爾拉癌症醫學公司 Chk1抑制劑之合成方法
US20240351992A1 (en) * 2021-08-17 2024-10-24 Glaxosmithkline Intellectual Property (No.3) Limited Preparation of p2x3 antagonist
WO2025101691A1 (en) 2023-11-08 2025-05-15 Exelixis, Inc. Methods for treating cancer using compounds that inhibit pkmyt1

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3773778A (en) 1972-01-24 1973-11-20 Squibb & Sons Inc Sulfur derivatives of pyrazolo (3,4-b)pyridines
IL112248A0 (en) 1994-01-25 1995-03-30 Warner Lambert Co Tricyclic heteroaromatic compounds and pharmaceutical compositions containing them
EP0836605B1 (en) 1995-07-06 2002-02-06 Novartis AG Pyrrolopyrimidines and processes for the preparation thereof
DE60221866T2 (de) 2001-10-19 2008-05-29 Ortho-Mcneil Pharmaceutical, Inc. 2-PHENYL BENZIMIDAZOLE UND IMIDAZO-i4,5ö-PYRIDINE ALS CDS1/CHK2-INHIBITOREN UND ADJUVANTIEN IN DER CHEMOTHERAPIE ODER STRAHLUNGSTHERAPIE ZUR BEHANDLUNG VON KREBS
JP5039268B2 (ja) 2001-10-26 2012-10-03 アベンティス・ファーマスーティカルズ・インコーポレイテツド ベンゾイミダゾールおよび類縁体および蛋白キナーゼ阻害剤としてのその使用
CA2464934A1 (en) 2001-10-31 2003-05-08 Bayer Healthcare Ag Pyrimido [4,5-b] indole derivatives
CA2484209C (en) * 2002-05-03 2013-06-11 Exelixis, Inc. Protein kinase modulators and methods of use
US7202244B2 (en) 2002-05-29 2007-04-10 Millennium Pharmaceuticals, Inc. Chk-1 inhibitors
WO2005011597A2 (en) 2003-07-29 2005-02-10 Irm Llc Compounds and compositions as protein kinase inhibitors
JP4758349B2 (ja) 2003-10-08 2011-08-24 アイアールエム・リミテッド・ライアビリティ・カンパニー タンパク質キナーゼ阻害剤としての化合物および組成物
ES2344007T3 (es) 2003-10-14 2010-08-16 The Arizona Board Of Regents On Behalf Of The University Of Arizona Inhibidores proteina quinasa.
US7691866B2 (en) 2003-10-16 2010-04-06 Novartis Vaccines And Diagnostics, Inc. 2,6-disubstituted quinazolines, quinoxalines, quinolines and isoquinolines and methods of their use as inhibitors of Raf kinase
US7163939B2 (en) 2003-11-05 2007-01-16 Abbott Laboratories Macrocyclic kinase inhibitors
US20050096324A1 (en) 2003-11-05 2005-05-05 Zhi-Fu Tao Macrocyclic kinase inhibitors
EP1742935B1 (en) 2004-04-13 2010-02-24 Icagen, Inc. Polycyclic pyrazines as potassium ion channel modulators
US20070054916A1 (en) 2004-10-01 2007-03-08 Amgen Inc. Aryl nitrogen-containing bicyclic compounds and methods of use
CA2604284A1 (en) 2005-04-28 2006-11-02 Supergen, Inc. Protein kinase inhibitors
EP1899322B1 (en) 2005-06-28 2009-09-02 Sanofi-Aventis Isoquinoline derivatives as inhibitors of rho-kinase
TW200804345A (en) 2005-08-30 2008-01-16 Novartis Ag Substituted benzimidazoles and methods of preparation
CA2624882C (en) 2005-10-06 2014-05-20 Schering Corporation Pyrazolopyrimidines as protein kinase inhibitors
US8119655B2 (en) 2005-10-07 2012-02-21 Takeda Pharmaceutical Company Limited Kinase inhibitors
GB0616747D0 (en) * 2006-08-24 2006-10-04 Astrazeneca Ab Novel compounds
AU2007338410B2 (en) 2006-12-27 2012-08-16 Sanofi-Aventis Cycloalkylamine substituted isoquinoline derivatives
CA2681015C (en) 2007-03-16 2016-06-21 The Scripps Research Institute Inhibitors of focal adhesion kinase
WO2008117050A1 (en) 2007-03-27 2008-10-02 Astrazeneca Ab Pyrazolyl-amino-substituted pyrazines and their use for the treatment of cancer
EP2170886A1 (en) 2007-07-02 2010-04-07 Cancer Research Technology Limited 9h-pyrimido[4,5-b]indoles, 9h-pyrido[4',3':4,5]pyrrolo[2,3-d]pyridines, and 9h-1,3,6,9-tetraaza-fluorenes as chk1 kinase function inhibitors
GB0719644D0 (en) 2007-10-05 2007-11-14 Cancer Rec Tech Ltd Therapeutic compounds and their use
GB0803018D0 (en) * 2008-02-19 2008-03-26 Cancer Rec Tech Ltd Therapeutic compounds and their use
JP6073910B2 (ja) 2011-11-09 2017-02-01 キャンサー・リサーチ・テクノロジー・リミテッド 5−(ピリジン−2−イル−アミノ)−ピラジン−2−カルボニトリル化合物及びその治療使用
JP6027230B2 (ja) * 2012-05-15 2016-11-16 キャンサー・リサーチ・テクノロジー・リミテッド 5−[[4−[[モルホリン−2−イル]メチルアミノ]−5−(トリフルオロメチル)−2−ピリジル]アミノ]ピラジン−2−カルボニトリルおよびその治療上の使用

Also Published As

Publication number Publication date
EP2855448B1 (en) 2017-02-08
AU2013261605A1 (en) 2014-11-13
US10259806B2 (en) 2019-04-16
US9663503B2 (en) 2017-05-30
US20180022739A1 (en) 2018-01-25
HK1203529A1 (en) 2015-10-30
CN106279142B (zh) 2019-05-03
CN106279142A (zh) 2017-01-04
US11787792B2 (en) 2023-10-17
KR20150023252A (ko) 2015-03-05
SG11201407238VA (en) 2014-12-30
JP2017036314A (ja) 2017-02-16
RU2014147105A (ru) 2016-07-10
KR20200038990A (ko) 2020-04-14
IL235133A (en) 2017-03-30
CN104302635B (zh) 2016-07-06
JP2015520753A (ja) 2015-07-23
CN104302635A (zh) 2015-01-21
CA2870837A1 (en) 2013-11-21
KR102635954B1 (ko) 2024-02-13
BR112014026801A2 (pt) 2017-06-27
PL2855448T3 (pl) 2017-09-29
ZA201408452B (en) 2016-08-31
ES2981584T3 (es) 2024-10-09
NZ702050A (en) 2016-08-26
MX2014012881A (es) 2015-04-08
KR20220151007A (ko) 2022-11-11
AU2017268508B2 (en) 2019-07-04
JP6027230B2 (ja) 2016-11-16
BR112014026801B1 (pt) 2022-03-03
KR20240023685A (ko) 2024-02-22
EP2855448A1 (en) 2015-04-08
ES2624307T3 (es) 2017-07-13
EP3210980A1 (en) 2017-08-30
EP3210980B1 (en) 2024-04-03
KR102090792B1 (ko) 2020-03-18
WO2013171470A1 (en) 2013-11-21
RU2659786C2 (ru) 2018-07-04
US20150126471A1 (en) 2015-05-07
HK1243408A1 (en) 2018-07-13
AU2013261605B2 (en) 2017-08-31
AU2017268508A1 (en) 2017-12-14
IN2014DN09221A (enExample) 2015-07-10
US20210276990A1 (en) 2021-09-09
JP6362652B2 (ja) 2018-07-25
KR20210047981A (ko) 2021-04-30
KR20210156333A (ko) 2021-12-24
DK2855448T3 (en) 2017-05-01
MX358819B (es) 2018-09-05
AU2017268508C1 (en) 2019-10-17
KR102246265B1 (ko) 2021-04-29
KR102341637B1 (ko) 2021-12-21

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